Methodology was developed to expand the range of benign alkyl glycoside surfactants to include also anionic types. This was demonstrated possible through conversion of the glycoside to its carboxyl derivative. Specifically, octyl β-D-glucopyranoside (OG) was oxidised to the corresponding uronic acid (octyl β-D-glucopyranoside uronic acid, OG-COOH) using the catalyst system T. versicolor laccase/2,2,6,6-tetramethylpiperidinyloxy (TEMPO) and oxygen from air as oxidant. The effects of oxygen supply methodology, concentrations of laccase, TEMPO and OG as well as reaction temperature were evaluated. At 10 mM substrate concentration, the substrate was almost quantitatively converted into product, and even at a substrate concentration of 60 mM, 85% conversion was reached within 24 h. The surfactant properties of OG-COOH were markedly dependent on pH. Foaming was only observed at low pH, while no foam was formed at pH values above 5.0. Thus, OG-COOH can be an attractive low-foaming surfactant, for example for cleaning applications and emulsification, in a wide pH range (pH 1.5-10.0).

中文翻译：

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pH反应性表面活性剂辛基β-D-吡喃葡萄糖苷糖醛酸的化学酶法合成。

开发了方法学以扩大良性烷基糖苷表面活性剂的范围，使其也包括阴离子类型。通过将糖苷转化为其羧基衍生物证明了这一点。具体而言，使用催化剂体系T. versicolor漆酶/ 2,2,6,6-四甲基哌啶基氧基将辛基β-D-吡喃葡萄糖苷（OG）氧化为相应的尿酸（辛基β-D-吡喃葡萄糖苷，OG-COOH）。 （TEMPO）和空气中的氧气作为氧化剂。评估了供氧方法，漆酶，TEMPO和OG的浓度以及反应温度的影响。在10 mM的底物浓度下，底物几乎定量地转化为产物，即使在60 mM的底物浓度下，在24小时内也达到了85％的转化率。OG-COOH的表面活性剂性质明显取决于pH值。仅在低pH下观察到泡沫，而在pH值高于5.0时未形成泡沫。因此，OG-COOH可以是一种有吸引力的低泡表面活性剂，例如在宽pH范围（pH 1.5-10.0）中用于清洁应用和乳化。